


A Pretty High Bar

by VictoryTofu



Category: Teen Wolf (TV)
Genre: Anal Play, Anal Sex, Dirty Talk, Fingerfucking, First Time, Jock Straps, Kissing, Loss of Virginity, M/M, Rimming, Socks
Language: English
Status: Completed
Published: 2013-01-11
Updated: 2013-01-11
Packaged: 2017-11-25 03:51:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,188
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/634823
Author URL: https://archiveofourown.org/users/VictoryTofu/pseuds/VictoryTofu
Summary: <blockquote class="userstuff">
              <p>Stackson Smut.  That's all.</p>
            </blockquote>





	A Pretty High Bar

**Author's Note:**

> Jax and Stiles, pretty simple. It's my first time writing sex, I hope it's good.

"Oh, sweet Jesus, that's unbelievable! nnhhh..." Stiles moaned into the high-thread count  navy blue sheets and fisted his hands next to his head. He was laying ass-up on his chest and knees, naked save for mismatched socks, which he refused to remove as he insisted the hardwood floors in the Whittemores' house were freezing cold.

Jackson was kneeling behind him, wearing only a grey jockstrap with green piping. His hands were spreading Stiles's ass cheeks, his tongue broad and lazily lapping at his hole. Stiles continued mumbling and Jackson absently thought that, even when he's not saying words and lost in a sex-daze, the skinny spaz can't shut up, and he loved it.

Language found Stiles again and he looked back over his shoulder, "You are always an overachiever, aren't you? Is there any skill you haven't mastered? Did you spend hours and hours practicing anilingus on a fleshlight or what? This is-EEP!"  Stiles was interrupted by a loud Smack on his right ass cheek, leaving a red shadow of Jackson's hand. A hand that was now smoothing over the sensitive skin and Jackson leaned back on his haunches.

"Babe, you need to relax and enjoy the moment, and Not monologue through sex, or I'll have to ball-gag you." Jackson raised an eyebrow and Stiles's cock twitched at the thought.  "Now, how about I get back to eating that tight little hole?" Stiles could swear he felt Jackson's smirk against his perenium as he nosed against his entrance, which puckered in anticipation.

"P-please do, Jax, I'll be good, you're just so-" Stiles forced himself to stop talking by biting his fist. Though he was interested in being gagged by the lacrosse captain, he didn't want him to stop The World's Best Rim-job.  Jackson responded with a chuckle and slowly drug his tongue from the base of Stiles's sack up to his asshole. Before, he'd only been licking the outside skin, tickling the dusting of hair; now he pointed his tongue and thrust into the opening.

Jackson alternated deep probing thrusts with sucking on the ring of muscle and gently nibbling at the soft hole. Stiles's muscles clenched and flexed around Jackson's tongue, causing sweat to bead on his back and his rock-hard cock to dribble precum.

Somehow Jackson sensed Stiles was leaking and swiped the fluid onto his finger, then reached up for Stiles's mouth.  He accepted it, sucking the bitter taste off of Jackson's perfectly manicured finger. Stiles stayed suckling on the finger like a pacifier as Jackson worked open his hole.  Jackson stroked Stiles's face with his thumb while Stiles moaned and keened with the sensation of having Jackson in both ends.  He removed this finger with a loud Pop and a quiet whine from Stiles.

"You wanna get opened up a little more? Jackson whispered against Stiles's hole.

Stiles shuddered out an "Ohgodyes," panting as if he'd been running suicides.  Jackson chucked and softly kissed the small of Stiles's back.  He massaged the taught muscles in Stiles's thighs, and continued kissing his way up to Stiles's nape.  When he was leaning across the other man, slotted like a puzzle, he wrapped one arm around Stiles's chest, the other reaching into his nightstand to retrieve a bottle of lube.

Stiles's mind was racing, more so than usual.  At the top of his mind was "Oh sweet satan, I'm having sexy times with the hottest dude in the history of hot dudes."  As Jackson wrapped himself around Stiles, he turned his head to lock Jackson in a kiss, slow and steaming.  This is when a new thought pushed it's way into Stiles's mind.  "Of all the ways I thought Jackson would act during sex(there had been many ways Stiles thought Jackson would act during sex) I never imagined he'd be so… sweet, gentle."

"Are you comfortable like this?" Jackson nibbled on Stiles's earlobe.

"I'd be more comfortable with someone in my ass," Stiles grinned back. Jackson let out a deep, hearty laugh and moved back between Stiles's calves, ass still pointed up in the air.

Stiles could feel Jackson's gaze.  "Jesus, Stiles, you look amazing like this, you're so fucking beautiful." Jackson drank in the sight of the other guy, exposed and needy.  He rubbed his left nipple between his fingers and adjusted his cock in his jockstrap where precum was staining the material a darker grey.

"Ha!" Stiles couldn't help but laugh and roll his eyes into the sheets. "You think I'm beautiful? Have you ever seen a mirror? I look like a mannequin that was assembled wrong compared to you."

"Stop it. Don't be like that, you were assembled perfectly," Jackson smiled and rubbed small circles with his fingers over Stiles's asks cheeks. "Has anyone ever been inside you before?" Jackson's voice was low and soft, even though no one else was home, and would likely be gone until early morning hours. It comforted Stiles, made him feel more connected to Jackson, somehow.

"I've, like, played around down there in the shower and stuff, but no one else has ever been involved, you know?" Stiles left out that no one else had ever been involved with him sexually, Ever, in any sort of way.  He didn't really think that Jackson would call him a virgin loser and tell him to put on some pants and never come back if he knew Stiles'd never even made out with anyone before this afternoon, but he didn't want to press his luck.

"Oh, that's pretty hot. Well, we don't have to do anything you don't want.  I mean, it can be weird the first time, and I don't want you to think, like, you have to do this, or whatever." Jackson sighed- he hated when he felt like he was rambling. "I just, I want you to feel good."

"Dude- I want this. And if I feel like you're gonna bust my O-ring I'll tap out, trust me." Stiles thought he should feel awkward, exposed as he was, eyes locked with Jackson over he shoulder and talking sex, but instead he felt warm and comfortable, and really Really turned on.

Jackson smirked- not his usual smirk full of resentment and arrogance, but one that let Stiles know he was going to do his best to blow Stiles's mind. "The trick is to keep breathing," Jackson whispered as he uncapped the bottle of lube and slicked up his fingers. He started by rubbing along Stiles's crack, ghosting over the hole he'd already sucked swollen and red. He slowly began circling the entrance. Stiles was breathing deeply, in and out, focussing all of his attention to where Jackson was touching him, left hand spread on his left ass cheek, a few fingers massaging around his hole, his knees between Stiles's calves, Jackson's hot breath steady on his skin.

Stiles sighed with contentment as Jackson slid his middle finger into his hole, slowly he began pumping in and out, just shy of his second knuckle. It was no further than his tongue had reached, but the feeling was enough to send Stiles's head spinning. "Oh, please, Jackson, please..." He mumbled, not knowing exactly what he was begging for. Jackson leaned down and kissed Stiles's hip in reply.

He continued like this, slowly massaging Stiles's ring of muscle until he began rocking back into the small thrusts. "Easy, babe, you ready for another finger?"

"Oh, god yes," Stiles panted in reply. He briefly through he should be embarrassed for being so wanton, but he was too turned on and desperate to even begin to worry about modesty. Jackson simply hummed in agreement and slid his index finger in. He used the two fingers to reach further past Stiles's ring to where he could feel his prostate. As soon as Jackson was able to rub the knot, Stiles saw stars.

"Holy shit, I can't feel my legs. Is that normal? Oh my god, I don't care if it's normal don't stop. On OH right there! Oh god, Jackson, you're magic. You're like a wizard or something. Oh..." Stiles couldn't help but ramble as Jackson massaged his prostate over and over with each thrust. Stiles's cock was leaking more precum than he'd known possible. He briefly felt bad for staining Jackson's sheets, but then again, Jackson's who has his in this state.

"God, you're so gorgeous like this, Stiles. Your fucking hole is perfect, you're so smooth and sweet, fuck. Can I add another finger?" Jackson was panting at this point as well, smile broad on his flushed face.

"Oh yes, god yes, I need more," Stiles was only vaguely aware of his reply, lost in the rolling sensations of his p-spot. Jackson took a moment to re-lube his fingers and set back to work, stretching Stiles wider than ever. He abandoned aiming for Stiles's prostate with each thrust and focused on a different pleasure. He scissored his fingers and slowly worked Stiles's asshole wider and wider still. "Oh, yes, that's amazing," Stiles  worried for a moment that his vocabulary was shrinking, but ignored that and focused on Jackson's hand and where it was reshaping his ass.

Jackson took a moment to appreciate the body before him. Thin and lithe, pale with moles dotting like constellations. Stiles's ass was a dream, smooth, white skin with just a dusting of hair, damp with lube. The meat of his cheeks made them stand out like two bubbles. His hole was pulled tight and smooth around Jackson's fingers. His thumb alternately rubbed Stiles's perineum and the dark skin just around his entrance. His sack hung, slowly swinging with Stiles's hips bucking against the pressure at his ass. Jackson could barely see the cock he knew was rock hard, but delighted in it none the less; all of this to the background noise of Stiles's moans and aborted attempts at begging for more.

"Feeling good, babe?" Jackson, for all the visual clues he was getting, longed to be told, in no uncertain terms, that he was doing a good job.

"Fuck me." Jackson froze. "Please, Jax, you're so hot, please fuck my ass." Stiles was whining at this point, which was an unexpected turn on for both of them.

"Oh, god, you have no idea how much I want that, Stiles." Jackson made an attempt to reach for the condoms spread haphazardly on his nightstand but Stiles reached out for his wrist.

"No, please, if it's alright, I mean, I want to feel you, all of you, in me."  Jackson stilled. "You're a werewolf now, you can't carry or get disease, right? So it's safe. I mean, if you don't want to..." Jackson silenced Stiles with a kiss that sucked the air out of him.

"You had no idea how much I want that, Stiles." Jackson rubbed the short buzz cut on his lover's head. "I also... If it's ok..."

"What? Tell me."

"I'd like to, have you on your back, so we can look at each other." Jackson could feel the heat from his blush spreading down his neck onto his chest. Stiles simply nodded and let himself be gently turned over in Jackson's strong arms. "Oh, god, I thought you were hot before..."

"As great as compliments feel, I'd rather feel your dick inside of me, so... Lose the strap, Jack," Stiles couldn't help but tease. His body felt so perfectly content and hungry and the same time. He hummed with the touch of Jackson, his hole was buzzing, anxious for more to fill it, Stiles never realized how much he hated being empty until Jackson was out of him. Jackson positioned Stiles carefully under him. He was flat on his back, legs spread as wide as he could get them, hole angled slightly up with his knees bent over Jackson's elbows.

The two locked eyes and Stiles couldn't hide his amazement.  Jackson could have been carved from marble. His cheekbones and jaw were impeccable. He had not an ounce of baby fat left, only strong, smooth muscles.  He was flushed enough that his freckles stood out more against the pink skin of his cheeks and shoulders. His nipples were small and erect, inviting Stiles to reach up and roll one between his fingers. Now that Jackson had removed his jockstrap, Stiles was free to wonder at his cock. Stiles was never embarrassed if his own, just a bit under average at about five, five and a half inches, but Jackson's looked positively awesome. It was at least three inches longer than his own, with girth to match. He was cut, with a slight upward arc to the tool. Stiles's mouth watered.

"See something you like?" Jackson smiled, actually smiled, at Stiles, without a hint of arrogance.  He leaned down over Stiles and caught him in a kiss. Softer than before, barely open-mouthed. Jackson thought Stiles tasted like candy and excitement. Stiles thought Jackson tasted like mint and frost. Both were more than pleased. Stiles opened his mouth wider, inviting Jackson in. Jackson felt like it was the answer to a question he didn't know how to ask.

They laid like that for a moment, chest to chest, kissing slowly and languidly until they needed air. "Please, Jax, please fuck me now. I need you so badly," Stiles was whispering the words against Jackson's cheek, and he felt the blunt head of Jackson's cock press against his hole, slick with lube and hungry for the man on top of him.

"Jackson took Stiles's face in his hands and looked him in the eye. "Tell me if I hurt you,"  then began sucking on Stiles's neck as his cock slid into him, Stiles moaned and his eyes rolled back in his head. As wonderful as Jackson's tongue had been and as exciting as his fingers were, neither compared to this. As soon as Jackson was fully seated in Stiles, he pulled off of his neck with a soft kiss. "Are you ok, Sti?" His pupils were blown wide, and big blue eyes were dripping with concern, or adoration, Stiles couldn't tell.

"I am really, Really ok, Jax." Stiles tried to smile but instead let his head fall back on the bed, sweat beading in his forehead. His hole felt so full, Jackson's cock was impossibly hot and hard, so perfect, Stiles wondered how he'd ever been happy without it in his ass. "I think I'm ready for you to... move, or whatever."

Jackson huffed a laugh and slowly began pumping his cock in and out of Stiles, feeling the rim of his asshole pull against his length. Stiles's hole was warm and smooth, slick and pliant thanks to the all the prep work they'd done. Jackson gradually built up his pace until his balls were slapping against Stiles's crack with each thrust. The bottom moaned and writhed under Jackson, clearly in ecstasy. Jackson's cock slamming against Stiles's prostate every third or fourth pump.

Stiles was hazing in and out of a blind mist of sex. He randomly mumbled phrases he heard in porn and assumed were never said in real life. "Oh, god, you're so big!" "Beat my Fucking hole!" "Fuck Me, Fuck Me, Fuck Me!" all spilled from his mouth with no thought. Jackson, for his part, felt so good he was barely able to keep a steady rhythm and focus on hitting Stiles's p-spot, let alone talk dirty.

It could have been hours, neither boy could keep track of time, but they worked themselves into a sweaty, panting blur. The steady sound of fucking mixed with unrestrained moans and the obscene noises of air and lube squelching in Stiles's hole, he reached down to feel where they were joined, and shuddered in amazement when he felt Jackson's cock and his rim slide against each other. His hole felt abused, worked out in a way he never knew existed, and he loved it. 

"Stiles, I'm close." Jackson whispered into his lover's ear. Stiles ran his hands down Jackson's sweat-slick back and grabbed his tight, round ass.

"Me, too, fuck, I... I want..." Stiles stuttered with hot, fast breaths.

"Babe, tell me," Jackson felt Stiles's hole clench and flex around his cock, while still doing his best to slam in and out of the sloppy, slick heat with some semblance of rhythm.

"Cum In Me." Stiles squeezed Jackson's ass and huffed. "I want you to come in me, I want to feel you squirt up my hole and," Stiles blushed, "and mark me as yours."

Jackson pulled back for just a second, noticing the pool of precum around Stiles's navel that was larger than most loads. He absently congratulated himself for aiming at Stiles's prostate so well before smothering Stiles's face. It wasn't really a kiss as much as Jackson talking into Stiles's mouth. "Jesus fuck yeah, so good, so tight, I'm gonna cum in your fucking cunt, fill your pussy 'ti you're bursting with my jizz. You're such a good little bottom, taking my fucking load, You're so fucking hot, Ohhh..."  Jackson's rant melted into a proper, sloppy kiss with Stiles.

A few thrusts later and Jackson was lost in ecstasy. He came with a moan into Stiles's mouth, and used all his strength to push his cock as far as he could, shooting his load as deep as possible. Stiles could feel the heat speeding even further into him and was done- he came with a shout as his vision whited out. Stiles felt that for minute, or  possibly a day, his whole universe was only the sensation of Jackson. His lips against his neck, his hands rubbing up and down Stiles's sides, and his cock- his huge cock that was still spurting aftershocks deep in his ass, with his hole stretched out around his base. He never felt more safe or more content. He wondered how long Jackson could stay inside of him. Maybe forever?

Jackson was in no rush to move, either. He felt Stiles's come sticky between their stomachs, and finished marking what he thought must be his tenth hicky on Stiles's neck and chest. Once their breathing came down to a resting pace, he chanced, "D-do you want me to pull out, now?"

"No!" Stiles was wide eyed, and Jackson smiled with relief. "I mean, if it's ok and not too needy or whatever, I just really like having your inside of me." Stiles seemed ashamed of his answer. Jackson simply hugged him closer and pushed his softening groin further against Stiles's worn out hole.

"Good. You were really great, you know." He traced random patterns on Stiles's face, playing connect the dots with his moles. "That was the best I've ever had, the best I've ever felt in my life." He punctuated it with a soft kiss between Stiles's eyes. 

"Me, too. I mean, you're my first, but… yeah, you set a pretty high bar for yourself." Stiles softly giggled and closed his eyes. Jackson curled into Stiles's neck, body still plastered atop him and arms wrapped around him like a straight jacket, and mumbled something that sounds like 'challenge accepted.' The both smiled and drifted off to sleep.

**Author's Note:**

> Thanks for reading. Stackson is my favorite pairing, but when they have sex in fics it's usually violent or mean-spirited or humiliating. I don't like that. Let me know your thoughts, I might make a multi-part story out of this.


End file.
